Acetic Acid → HCID 19743090, compound

HRID 2254671Notes

Reaction equation

HRID 2254671 reaction equation
C(#N)C[CH2:3][CH2:4][O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].Cl.[C:16]([OH:19])(=[O:18])[CH3:17]>>[C:16]([OH:19])(=[O:18])[CH2:17][CH2:3][CH2:4][O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 19743089HCID 19743089, compound

Product 1

HCID 19743090HCID 19743090, compoundYield 32%

Procedure

A solution of 5-oxatridecanonitrile (1.90 g, 9.6 mmol) in a mixture of acetic acid (10 mL) and concentrated HCl (50 mL) was refluxed for 20 h. After evaporation of the solvent in vacuo, water (50 mL) and ethyl acetate (100 mL) were added to the residue. The organic phase was washed with water (2×50 mL), brine (1×50 mL), and then dried over Na2SO4. After distillation (Kugelrohr device, 120°-125° C./0.1 torr) and column chromatography (silica gel) using ethyl acetate:hexane (1:1) as eluent. 5-Oxatridecanoic acid (0.66 g, 32%) was isolated as a colorless oil. IR: 3550-2300, 1700 cm-1, 1H-NMR: 0.78-0.98 (t, 3H), 1.00-1.40 (m, 10H), 1.42-1.62 (p, 2H), 1.82-1.94 (p, 2H), 2.40-2.56 (t, 2H), 3.38-3.52 (m, 4H). Anal. Calcd. for C12H24O3 : C, 66.63, H, 11.18%; Found: C, 66.53, H, 11.14%.

Workup

  1. temperaturewas refluxed for 20 h
  2. customAfter evaporation of the solvent in vacuo, water (50 mL) and ethyl acetate (100 mL)
  3. additionwere added to the residue
  4. washThe organic phase was washed with water (2×50 mL), brine (1×50 mL)
  5. dry with materialdried over Na2SO4
  6. distillationAfter distillation (Kugelrohr device, 120°-125° C./0.1 torr) and column chromatography (silica gel)

Sources & evidence

ORD record
ord-a62597b761784003b5dfd717930f93b1
Source dataset
uspto-grants-1993_08
Patent number
US05236955

Reaction notes

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